Phenyl isocyanate → HCID 21184658, compound

HRID 567969Notes

Reaction equation

HRID 567969 reaction equation
[N+:1]([C:4]1[CH:10]=[CH:9][C:7]([NH2:8])=[C:6]([NH:11][S:12]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)(=[O:14])=[O:13])[CH:5]=1)([O-:3])=[O:2].[C:21]1([N:27]=[C:28]=[O:29])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>>[N+:1]([C:4]1[CH:10]=[CH:9][C:7]([NH:8][C:28]([NH:27][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[O:29])=[C:6]([NH:11][S:12]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)(=[O:14])=[O:13])[CH:5]=1)([O-:3])=[O:2]

Participants

3

Reactant 2

HCID 7672Phenyl isocyanateHCID 13109537HCID 13109537, compound

Product 1

HCID 21184658HCID 21184658, compound

Procedure

N-(4-Nitro 2-(phenylsulfonylamino)phenyl)-N′-phenylurea was prepared from 4-nitro 2-(phenylsulfonylamino)aniline(82 mg) and phenyl isocyanate(33 mg) by method A. The reaction was cooled and then partitioned between saturated ammonium chloride and 9:1 methylene chloride and methanol. The organic phase was dried over magnesium sulfate, filtered and concentrated in vacua. The residue was purified by column chromatography (ethyl acetate/hexanes) to afford desired(30.8 mg, 26%). EI-MS m/z 413(M+H)+.

Workup

  1. temperatureThe reaction was cooled
  2. custompartitioned between saturated ammonium chloride and 9:1 methylene chloride and methanol
  3. dry with materialThe organic phase was dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacua
  6. customThe residue was purified by column chromatography (ethyl acetate/hexanes)
  7. customto afford

Sources & evidence

ORD record
ord-5fae15649e454d8a939d22eb966fda84
Source dataset
uspto-grants-2001_01
Patent number
US06180675B2

Reaction notes

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